HU189348B - Process for producing l-/bis/hydroxy-methyl/-methyl/-3,4-dihydro- or 1,2,3,4-tetrahydro-isoquinolin derivatives - Google Patents
Process for producing l-/bis/hydroxy-methyl/-methyl/-3,4-dihydro- or 1,2,3,4-tetrahydro-isoquinolin derivatives Download PDFInfo
- Publication number
- HU189348B HU189348B HU833651A HU365183A HU189348B HU 189348 B HU189348 B HU 189348B HU 833651 A HU833651 A HU 833651A HU 365183 A HU365183 A HU 365183A HU 189348 B HU189348 B HU 189348B
- Authority
- HU
- Hungary
- Prior art keywords
- methyl
- formula
- hydroxymethyl
- bis
- dihydroisoquinoline
- Prior art date
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 11
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- -1 alkali metal alkoxide Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- 239000013638 trimer Substances 0.000 claims description 3
- JZZLDIIDMFCOGF-UHFFFAOYSA-N 1-methyl-3,4-dihydroisoquinoline Chemical class C1=CC=C2C(C)=NCCC2=C1 JZZLDIIDMFCOGF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- HMZNFQZDZQFVEP-UHFFFAOYSA-N 2-(3,4-dihydroisoquinolin-1-yl)propane-1,3-diol Chemical class C1=CC=C2C(C(CO)CO)=NCCC2=C1 HMZNFQZDZQFVEP-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VASUQTGZAPZKFK-UHFFFAOYSA-N 6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline Chemical compound C1CN=C(C)C2=C1C=C(OC)C(OC)=C2 VASUQTGZAPZKFK-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- PBYMYAJONQZORL-UHFFFAOYSA-N 1-methylisoquinoline Chemical compound C1=CC=C2C(C)=NC=CC2=C1 PBYMYAJONQZORL-UHFFFAOYSA-N 0.000 description 3
- UXBKURBVFSAMJC-UHFFFAOYSA-N 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)propane-1,3-diol Chemical compound C1CN=C(C(CO)CO)C2=C1C=C(OC)C(OC)=C2 UXBKURBVFSAMJC-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- DCHTVVOZNGBLBW-UHFFFAOYSA-N 1-(1,3-dihydroxypropan-2-yl)-3,4-dihydroisoquinoline-6,7-diol hydrobromide Chemical compound Br.OC1=C(O)C=C2C(C(CO)CO)=NCCC2=C1 DCHTVVOZNGBLBW-UHFFFAOYSA-N 0.000 description 2
- UXBHGTXVTUQRDW-UHFFFAOYSA-N 2-isoquinolin-1-ylethanol Chemical class C1=CC=C2C(CCO)=NC=CC2=C1 UXBHGTXVTUQRDW-UHFFFAOYSA-N 0.000 description 2
- NSLJVQUDZCZJLK-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydroisoquinoline Chemical compound C1CN=CC2=C1C=C(OC)C(OC)=C2 NSLJVQUDZCZJLK-UHFFFAOYSA-N 0.000 description 2
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- KKCVBYNOTLIZBF-UHFFFAOYSA-N 2-(6,7-diethoxy-3,4-dihydroisoquinolin-1-yl)propane-1,3-diol Chemical class C1CN=C(C(CO)CO)C2=C1C=C(OCC)C(OCC)=C2 KKCVBYNOTLIZBF-UHFFFAOYSA-N 0.000 description 1
- FCRBZLNRNVIYAQ-UHFFFAOYSA-N 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)propane-1,3-diol;hydrobromide Chemical compound Br.C1CN=C(C(CO)CO)C2=C1C=C(OC)C(OC)=C2 FCRBZLNRNVIYAQ-UHFFFAOYSA-N 0.000 description 1
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 1
- HTMGQIXFZMZZKD-UHFFFAOYSA-N 5,6,7,8-tetrahydroisoquinoline Chemical compound N1=CC=C2CCCCC2=C1 HTMGQIXFZMZZKD-UHFFFAOYSA-N 0.000 description 1
- IOPIDDLIIVFOGD-UHFFFAOYSA-N 6,7-diethoxy-1-methyl-3,4-dihydroisoquinoline Chemical compound C1CN=C(C)C2=C1C=C(OCC)C(OCC)=C2 IOPIDDLIIVFOGD-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000000141 anti-hypoxic effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Nanotechnology (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Physics & Mathematics (AREA)
- Mathematical Physics (AREA)
- Theoretical Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Transplantation (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU833651A HU189348B (en) | 1983-10-25 | 1983-10-25 | Process for producing l-/bis/hydroxy-methyl/-methyl/-3,4-dihydro- or 1,2,3,4-tetrahydro-isoquinolin derivatives |
| CA000466328A CA1237432A (en) | 1983-10-25 | 1984-10-25 | Isoquinoline derivatives, process for their preparation and pharmaceutical compositions containing them |
| DK508384A DK508384A (da) | 1983-10-25 | 1984-10-25 | Isoquinolinderivater, fremgangsmaade til fremstilling deraf og farmaceutisk praeparat indeholdende dem |
| AT84112856T ATE34740T1 (de) | 1983-10-25 | 1984-10-25 | (bis(hydroxymethyl)methyl)-isochinolinderivate, verfahren zu ihrer herstellung und pharmazeutische zubereitungen, die sie enthalten. |
| JP59223090A JPS60132961A (ja) | 1983-10-25 | 1984-10-25 | イソキノリン誘導体 |
| EP84112856A EP0143333B1 (en) | 1983-10-25 | 1984-10-25 | [Bis(hydroxymethyl)-methyl]-isoquinoline derivatives, process for preparing them and pharmaceutical compositions containing them |
| FI844184A FI79100C (fi) | 1983-10-25 | 1984-10-25 | Isokinolinderivat och foerfarande foer framstaellning daerav. |
| US06/664,842 US4656179A (en) | 1983-10-25 | 1984-10-25 | Isoquinoline derivatives, and pharmaceutical compositions containing them |
| AR29837684A AR241490A1 (es) | 1983-10-25 | 1984-10-25 | Procedimiento para preparar derivados de isoquinolina. |
| DE8484112856T DE3471654D1 (en) | 1983-10-25 | 1984-10-25 | Ûbis(hydroxymethyl)-methyl¨-isoquinoline derivatives, process for preparing them and pharmaceutical compositions containing them |
| AR30989088A AR241494A1 (es) | 1983-10-25 | 1988-01-22 | Procedimiento para preparar nuevos derivados de isoquinolina. |
| AR30989188A AR241497A1 (es) | 1983-10-25 | 1988-01-22 | Procedimiento para preparar nuevos derivados de 1,3-oxazino (4,3-a) isoquinolina. |
| AR30989288A AR241496A1 (es) | 1983-10-25 | 1988-01-22 | Procedimiento para preparar nuevos derivados de 2h-azeto(2,1-a)isoquinolina. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU833651A HU189348B (en) | 1983-10-25 | 1983-10-25 | Process for producing l-/bis/hydroxy-methyl/-methyl/-3,4-dihydro- or 1,2,3,4-tetrahydro-isoquinolin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU189348B true HU189348B (en) | 1986-06-30 |
Family
ID=10964920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU833651A HU189348B (en) | 1983-10-25 | 1983-10-25 | Process for producing l-/bis/hydroxy-methyl/-methyl/-3,4-dihydro- or 1,2,3,4-tetrahydro-isoquinolin derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4656179A (enrdf_load_html_response) |
| EP (1) | EP0143333B1 (enrdf_load_html_response) |
| JP (1) | JPS60132961A (enrdf_load_html_response) |
| AT (1) | ATE34740T1 (enrdf_load_html_response) |
| CA (1) | CA1237432A (enrdf_load_html_response) |
| DE (1) | DE3471654D1 (enrdf_load_html_response) |
| DK (1) | DK508384A (enrdf_load_html_response) |
| FI (1) | FI79100C (enrdf_load_html_response) |
| HU (1) | HU189348B (enrdf_load_html_response) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU189348B (en) * | 1983-10-25 | 1986-06-30 | Richter Gedeon Vegyeszeti Gyar Rt.,Hu | Process for producing l-/bis/hydroxy-methyl/-methyl/-3,4-dihydro- or 1,2,3,4-tetrahydro-isoquinolin derivatives |
| US10361802B1 (en) | 1999-02-01 | 2019-07-23 | Blanding Hovenweep, Llc | Adaptive pattern recognition based control system and method |
| US8352400B2 (en) | 1991-12-23 | 2013-01-08 | Hoffberg Steven M | Adaptive pattern recognition based controller apparatus and method and human-factored interface therefore |
| US7966078B2 (en) | 1999-02-01 | 2011-06-21 | Steven Hoffberg | Network media appliance system and method |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1036419A (en) * | 1964-09-22 | 1966-07-20 | Roche Products Ltd | A process for the manufacture of isoquinoline derivatives |
| GB1386076A (en) * | 1971-06-03 | 1975-03-05 | Wyeth John & Brother Ltd | Isoquinoline derivatives |
| HU189348B (en) * | 1983-10-25 | 1986-06-30 | Richter Gedeon Vegyeszeti Gyar Rt.,Hu | Process for producing l-/bis/hydroxy-methyl/-methyl/-3,4-dihydro- or 1,2,3,4-tetrahydro-isoquinolin derivatives |
-
1983
- 1983-10-25 HU HU833651A patent/HU189348B/hu not_active IP Right Cessation
-
1984
- 1984-10-25 AT AT84112856T patent/ATE34740T1/de not_active IP Right Cessation
- 1984-10-25 FI FI844184A patent/FI79100C/fi not_active IP Right Cessation
- 1984-10-25 JP JP59223090A patent/JPS60132961A/ja active Granted
- 1984-10-25 US US06/664,842 patent/US4656179A/en not_active Expired - Fee Related
- 1984-10-25 CA CA000466328A patent/CA1237432A/en not_active Expired
- 1984-10-25 EP EP84112856A patent/EP0143333B1/en not_active Expired
- 1984-10-25 DE DE8484112856T patent/DE3471654D1/de not_active Expired
- 1984-10-25 DK DK508384A patent/DK508384A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FI844184L (fi) | 1985-04-26 |
| US4656179A (en) | 1987-04-07 |
| FI79100C (fi) | 1989-11-10 |
| CA1237432A (en) | 1988-05-31 |
| DK508384A (da) | 1985-04-26 |
| DK508384D0 (da) | 1984-10-25 |
| FI844184A0 (fi) | 1984-10-25 |
| FI79100B (fi) | 1989-07-31 |
| DE3471654D1 (en) | 1988-07-07 |
| EP0143333B1 (en) | 1988-06-01 |
| EP0143333A1 (en) | 1985-06-05 |
| ATE34740T1 (de) | 1988-06-15 |
| JPH0414664B2 (enrdf_load_html_response) | 1992-03-13 |
| JPS60132961A (ja) | 1985-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |